US10721929B2 - Heterocyclic compound and harmful-arthropod-controlling agent containing same - Google Patents

Heterocyclic compound and harmful-arthropod-controlling agent containing same Download PDF

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US10721929B2
US10721929B2 US16/333,166 US201716333166A US10721929B2 US 10721929 B2 US10721929 B2 US 10721929B2 US 201716333166 A US201716333166 A US 201716333166A US 10721929 B2 US10721929 B2 US 10721929B2
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halogen atoms
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US20190223436A1 (en
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Kohei ORIMOTO
Masaru Shimomura
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to a heterocyclic compound and a harmful-arthropod-controlling agent using the same.
  • An Object of the present invention is to provide, a compound having excellent controlling efficacy on harmful arthropods.
  • the present invention is as follows.
  • Q represents a group represented by Formula Q1, a group represented by Formula Q2, or a group represented by Formula Q3,
  • n 0, 1, or 2
  • G 1 represents a nitrogen atom or CR 3a ,
  • G 2 represents a nitrogen atom or CR 3b ,
  • G 3 represents a nitrogen atom or CR 3c ,
  • G 4 represents a nitrogen atom or CR 3d ,
  • R 3a , R 3b , R 3c , and R 3d each independently represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group E, a phenyl group optionally having one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group H, OR 12x , NR 11 R 12 , NR 11a R 12a , NR 29 NR 12 , NR 29 OR 11 , NR 11 C(O)R 13 , NR 29 NR 11 C(O)R 13 , NR 11 C(O)OR 14 , NR 29 NR 11 C(O)OR 14 , NR 11 C(O)NR 15x R 16x , NR 24 NR 11 C(O)NR 15x R 16x , N ⁇ CHNR 15x R 16x , N
  • x 0 or 1
  • a 1 represents NR 5 , an oxygen atom, or a sulfur atom
  • a 2 represents a nitrogen, atom or CR 4a ,
  • a 3 represents a nitrogen atom or CR 4b ,
  • a 4 represents a nitrogen atom or CR 4c ,
  • R 4a , R 4b , and R 4c each independently represents a hydrogen, atom, a C1-C6 chain hydrocarbon group optionally, having one or more halogen atoms, a nitro group, OR 18 , NR 18 R 19 , a cyano group, or a halogen atom,
  • T represents a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alloy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O) m R 1 , OS(O) 2 R 1 , CH 2 OR 1 ,
  • X 1 represents a nitrogen atom or CR 1a ,
  • X 2 represents a nitrogen atom or CR 1b ,
  • X 3 represents a nitrogen atom or CR 1c ,
  • X 4 represents a nitrogen atom or CR 1d ,
  • X 5 represents a nitrogen atom or CR 1e ,
  • R 1x represents OR 7 , OS(O) 2 R 7 , S(O) m R 7 , NR 1 R 29 , NR 8 S(O) 2 R 7 , a C1-C5 chain hydrocarbon group having one or more halogen atoms, or a halogen atom,
  • R 1a , R 1b , R 1c , R 1d and R 1c each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom,
  • Y 1 represents NR 25 , an oxygen atom, or a sulfur atom
  • Y 2 represents a nitrogen atom or CR 26 ,
  • Y 3 represents a nitrogen atom or CR 27 ,
  • Y 4 represents a nitrogen atom or CR 28 .
  • R 5 and R 25 each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6, alkoxy group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, or a (C3-C7 cycloalkyl) C1-C6 alkyl group optionally having one or more halogen atoms,
  • R 26 , R 27 , and R 28 each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen-atom,
  • R 1y represents OR 7 , OS(O) 2 R 7 , S(O) m R 7 , NR 8 S(O) 2 R 7 , cyano group, a C1-C5 chain hydrocarbon group having ones or more halogen atoms, or a halogen atom,
  • R 1ay and R 7 each independently represents a C1-C6 chain hydrocarbon group having one or more halogen atoms
  • R 8 represents a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • n 0, 1, or 2
  • R 1 represents a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl)-C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G,
  • R 2 represents a cyclopropyl group, a cyclopropylmethyl group, or a C1-C6 group optionally having one or more halogen-atoms,
  • R 11 , R 17 , R 19 , R 24 , and R 29 each independently represents a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having-one or more halogen atoms,
  • R 30 represents a hydrogen atom, a halogen atom, OR 31 , NR 32 R 33 , or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 18 and R 31 each independently represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms
  • R 32 and R 33 each independently represents a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 12 represents a hydrogen atom, S(O) 2 R 23 , a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a C1-C6 alkyl group having one substituent selected from group F,
  • R 12x represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected, from Group F, a C3-C7 cycloalkyl group optionally having, one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally having one or more substituents selected from Group J, a phenyl group, a 6-membered aromatic heterocyclic group, in which the phenyl group and the 6-Membered aromatic heterocyclic group each independently optionally has one or more substituents selected from Group D,
  • R 23 represents a C1-C6 chain hydrocarbon groups optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D,
  • R 11a and R 12a together with the nitrogen atom which R 11a and R 12a are bonded, represent a 3- to 7-membered non-aromatic heterocyclic group, optionally having one more substituents selected from Group E,
  • R 13 represents a hydrogen-atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen, atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D.
  • R 14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group, in which the phenyl moiety in the phenyl C1-C3 alkyl group optionally has one or more substituents selected from Group D,
  • R 15 and R 16 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms
  • R 15x represents, a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,
  • R 16x represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group. J, or a hydrogen atom,
  • Group B a group consisting or a C1-C6 alkoxy group-optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more, halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen, atom,
  • Group C a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group, optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogenatoms, and halogen atom,
  • Group D a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, NHR 21 , NR 21 R 22 , C(O)R 21 , OC(O)R 21 , C(O)OR 21
  • Group E a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group,
  • Group F a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, NHR 21 , NR 21 R 22 , a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group C,
  • Group G a group consisting of a halogen atom and a C1 haloalkyl group
  • Group H a group consisting of a halogen atom, a nitro group, a cyano group, an amino group, a 5- or 6-membered aromatic heterocyclic group, a C1-C6 alkyl group optionally having one or more halogen atoms, OR 10 , NR 9 R 10 , C(O)R 10 , C(O)NR 9 R 10 , OC(O)R 9 , OC(O)OR 9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , and C(O)OR 10 ,
  • Group J a group consisting of C1-C6 alkyl group optionally having one or more halogen atoms, a halogen atom, and a cyano group,
  • R 9 represents a C1-C6 all group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms, and
  • R 10 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms.
  • Q is a group represented by Formula Q1, a group represented by Formula Q2, or a group represented by Formula Q3,
  • n 0, 1, or 2
  • G 1 is a nitrogen atom or CR 3a ,
  • G 2 is a nitrogen atom or CR 3b ,
  • G 3 is a nitrogen atom or CR 3c ,
  • G 4 is a nitrogen atom, or CR 3d ,
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C 6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group 8, a phenyl group optionally having one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected front Group H, OR 12 , NR 11 R 12 , NR 11a R 12a , NR 29 NR 12 , NR 29 OR 11 , NR 11 C(O)R 13 , NR 29 NR 11 C(O)R 13 , NR 11 C(O)OR 14 , NR 29 NR 11 C(O)OR 14 , NR 11 C(O)NR 15x R 16x , NR 24 NR 11 C(O)NR 15 R 16 , N ⁇ CHNR 15 R 16 , N ⁇ S(O)
  • x is 0 or 1
  • a 1 is NR 5 , an oxygen atom, or a sulfur atom,
  • a 2 is a nitrogen atom or CR 4a ,
  • a 3 is a nitrogen atom or CR 4b ,
  • a 4 is a nitrogen atom or CR 4c ,
  • R 4a , R 4b , and R 4c are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a nitro group, OR 18 , NR 18 R 19 , a cyano group, or a halogen atom,
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 allylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents-selected from Group G, OR 1 , S(O) m R 1 , OS(O) 2 R 1 , CH 2
  • X 1 is a nitrogen atom or CR 1a ,
  • X 2 is a nitrogen atom or CR 1b ,
  • X 3 is a nitrogen atom or CR 1c ,
  • X 4 is a nitrogen atom or CR 1d ,
  • X 5 is a nitrogen atom or CR 1e ,
  • R 1x is OR 7 , OS(O) 2 R 7 , S(O) m R 7 , NR 1 R 29 , NR 8 S(O) 2 R 7 , a C1-C5 chain hydrocarbon group having one or more halogen atoms, or a halogen atom,
  • R 1a , R 1b , R 1c , R 1d , and R 1c are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom,
  • Y 1 is NR 25 , an oxygen atom, or a sulfur atom
  • Y 2 is a nitrogen atom or CR 26 ,
  • Y 3 is a nitrogen atom or CR 27 ,
  • Y 4 is a nitrogen atom or CR 28 ,
  • R 5 and R 25 are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, or a (C3-C7 cycloalkyl) C1-C6 group optionally having one or more halogen atoms,
  • R 26 , R 27 , and R 28 are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom,
  • R 1ay is OR 7 , OS(O) 2 R 7 , S(O) m R 7 , NR 8 S(O) 2 R 7 , a cyano group, a C1-C5 chain hydrocarbon group having one or more halogen atoms, or halogen atom,
  • R 1ay and R 7 are each, independently a C1-C6 chain hydrocarbon group having one or more halogen atoms,
  • R 8 is a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • n 0, 1, or 2
  • R 1 is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen, atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G. or a C3-C7 cycloalkyl group having one or more substituents selected from Group G,
  • R 2 is a cyclopropyl group, a cyclopropylmethyl group, or a C1-C6 alkyl group optionally having one or more halogen atoms,
  • R 11 , R 17 , R 19 , R 24 , and R 29 are each independently a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 30 is a hydrogen atom, a halogen atom, OR 31 , NR 32 R 33 or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 18 and R 31 are each independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 32 and R 33 are each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
  • R 12 is a hydrogen, atom, S(O) 2 R 23 , a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a C1-C6 alkyl group having one substituent selected from Group F,
  • R 23 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D,
  • R 11a and R 12a together with the nitrogen atom to which R 11a and R 12a are bonded, are a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group E,
  • R 13 is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen, atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl-group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D,
  • R 14 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one halogen atoms, or a phenyl C1-C3 alkyl group, in which the phenyl moiety in, the phenyl C1-C3 alkyl group optionally has one or more substituents selected from Group D,
  • R 15 and R 16 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • Group B a group consisting of a C1-C6 alkoxy group-optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group, optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom,
  • Group C a group consisting of a C1-C6, chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen-atoms, a C3-C6 alkynyloxy group optionally having-one or more halogen-atoms, and a halogen atom,
  • Group D a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more-halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, NHR 21 , NR 21 R 22 , C(O)R 21 , OC(O)R 21 , C(O)OR 21
  • Group E a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a halogen atom an oxo group, a hydroxy group, a cyano group, and a nitro group,
  • Group F a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group NHR 21 , NR 21 R 22 , cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group C,
  • Group G a group consisting of a halogen atom and a C1-C6 haloalkyl group
  • Group H a group consisting of a halogen atom a nitro group, a cyano group, an amino group, a 5- or 6-membered aromatic heterocyclic group, a C1-C6 alkyl group optionally having one or more halogen atoms, OR 10 , NR 9 R 10 , C(O)R 10 , C(O)NR 9 R 10 OC(O)R 9 , OC(O)OR 9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , and C(O)OR 10 ,
  • R 9 is a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms, and
  • R 10 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms.
  • Q is a group represented by Formula Q1.
  • a 2 is CR 4a and A 4 is CR 4c ,
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is CR 4c .
  • a 2 is CR 4a
  • a 3 is a nitrogen atom
  • a 4 is CR 4c .
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 .
  • T is OR 1
  • R 1 is a C1-C5 alkyl group having three or more fluorine atoms.
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H, an amino group, NR 11 C(O)OR 14 , a hydrogen atom, or a halogen atom, and R 4a and R 4c are hydrogen atoms.
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogenatoms, or a hydrogen atom
  • R 4a and R 4c are hydrogen atoms.
  • R 2 is an ethyl group.
  • a harmful-arthropod-controlling composition containing:
  • a method for controlling a harmful arthropod including:
  • halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • substituents means having or not having a substituent. In a case of having two or more substituents, such substituents may be the same or different from each other.
  • halogen atom means having or not-having a halogen atom. In a case of having two or more halogen atoms such halogen atoms may be the same or different from each other.
  • an upper limit of the number of the substituents can be determined by the number of chemically substitutable hydrogen atoms.
  • an upper limit of the number of the halogen atoms can be determined by the number of chemically substitutable hydrogen atoms.
  • CX-CY in the present specification means that the number of carbon atoms is X to Y.
  • C1-C4 means that the number of carbon atoms is 1 to 4.
  • chain hydrocarbon group refers to an alkyl group, an alkenyl group, or an alkynyl group.
  • a case where the “chain hydrocarbon group” is an alkenyl group or an alkynyl group means that the number of carbon atoms is two or more.
  • alkyl group for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a secbutyl group a tert-butyl group, a pentyl group, a hexyl group, and an octyl group can be mentioned, and exemplification is made depending on the above-mentioned range of the number of carbon atoms.
  • alkenyl group for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group, a 5-hexenyl group, and a 7-octenyl group can be mentioned, and exemplification is made depending on the above-mentioned range of the number of carbon atoms.
  • alkynyl group for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-ethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, a 5-hexynyl group, and a 7-octynyl group can be mentioned, and exemplification is made depending on the above-mentioned range of the number of carbon atoms.
  • C1-C1.0 chain hydrocarbon group having one or more halogen atoms refers to a C1-C10 alkyl group having one or more halogen atoms, a C2-C10 alkenyl group having one or more halogen atoms, or a C2-C10 alkynyl group having one or more halogen atoms.
  • a C1-C10 alkyl group having one or more halogen atoms is preferable.
  • C1-C10 alkyl group having one or more halogen atoms for example, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2-bromo-1,1,2,2-tetrafluoroethyl group, a perfluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a 2,2,3,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, a 1-methyl-2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a perfluorobutyl group, a perfluoropentyl group, and a perfluorohexyl group can be mentioned.
  • C1-C6 haloalkyl group for example, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 2-bromo-1,1,2,2-tetrafluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a 1-methyl-2,2,3,3-tetrafluoropropyl group, and a perfluorohexyl group can be mentioned.
  • cycloalkyl group for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group can be mentioned, and exemplification is, made depending on the above-mentioned range of the number of carbon atoms.
  • alkoxy group refers to an alkoxy group having the alkyl group, and, for example, a methoxy group, an ethoxy-group, a propoxy group, an isopropoxy group, a 1,1-dimethylpropoxy group, a 1,2-dimethylpropoxy group, a 1-ethylpropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group can be mentioned.
  • alkylsultfanyl group refers to an alkylsulfanyl group having the alkyl group, and, for example, a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a 1,1-dimethylpropylsulfanyl group, a 1,2-dimethylpropylsulfanyl group, a 1-ethylpropylsulfanyl group, and a butylsulfanyl group can be mentioned.
  • alkylsulfinyl group refers to an alkylsulfinyl group having the alkyl group, and, for example, a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a 1,1-dimethylpropylsulfinyl group, a 1,2-dimethylpropylsulfinyl group, a 1-ethylpropylsulfinyl group, and a butylsulfinyl group can be mentioned.
  • alkylsulfonyl group refers to an alkylsulfonyl group having the alkyl group, and, for example, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a 1,1-dimethylpropylsulfonyl group, a 1,2-dimethylpropylsulfonyl group, a 1-ethylpropylsulfonyl group, and a butylsulfonyl group can be mentioned.
  • 3- to 7-membered non-aromatic heterocyclic group refers to a group that contains an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a dihydropyridine ring, a tetrahydropyridine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyriinidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazoiidinering, a 1,3-oxizinane ring, a morpholiite ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thia
  • (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms refers to a group in which (C1-C alkoxy) and/or (C2-C5 alkyl) has one or more halogen atoms, and, for example, a 2-(trifluoromethoxy) ethyl group, 2,2-difluoro-3-methoxypropyl, a 2,2-difluoro-3-(2,2,2-trifluoroethoxy) propyl group, and a 3-(2-chloroethoxy) propyl group can be mentioned.
  • (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms refers to a group in which (C1-C5 alkylsulfanyl) and/or (C2-C5 alkyl) has one or more halogen atoms, and, for example, a 2,2-difluoro-2-(trifluoromethylthio) ethyl group can be mentioned.
  • (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms refers to a group in which (C1-C5 alkylsulfinyl) and/or (C2-C5 alkyl) has one or more halogen atoms, and, for example, a 2,2-difluoro-2-(trifluoromethanesulfinyl) ethyl group can be mentioned.
  • (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms refers to a group in which (C1-C5 alkylsulfonyl) and/or (C2-C5 alkyl) has one or more halogen atoms, and, for example, a 2,2-difluoro-2-(trifluoromethanesulfonyl) ethyl group can be mentioned.
  • (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms refers to a group in which (C3-C6 cycloalkyl) and/or (C1-C3 alkyl) optionally has one or more halogen atoms, and, for example, a (2,2-difluorocyclopropyl) methyl group, a 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and a 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group can be mentioned.
  • (C3-C7 cycloalkyl) C1-C6 alkyl group optionally having one or more halogen atoms refers to a group in which (C3-C7 cycloalkyl) and/or (C1-C6 alkyl) optionally has one or more halogen atoms, and, for example, a (2,2-difluorocyclopropyl) methyl group, a 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, a 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group, and a 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoropropyl group.
  • (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G refers to a group in which (C3-C7 cycloalkyl) and/or (C1-C3 alkyl) has one or more substituents selected from one or more Group G, and, for example, a (2,2-difluorocyclopropyl)-methyl group, a [1-(trifluoromethiyl)cyclopropyil]methyl group, a [2-(trifluotomethyl)cyclopropyl]methyl group, a 2-cylopropyl-1,1,2,2-tetrafluoroethyl group, a 2-cyclopropyl-3,3,3-trifluoropropyl group, and a 1,1,2,2-tetrafluoro-2-[2-(trifluoromethyl)cyclopropyl]ethyl group can be mentioned.
  • C3-C7 cycloalkyl group having one or more substituents selected from Group G for example, a 2,2-difluorocyclopropyl group, a 1-(2,2,2-trifluoroethyl)cyclopropyl group, and a 4-(trifluoromethyl)cyclohexyl group can be mentioned.
  • phenyl C1-C3 alkyl group in which the phenyl moiety in the phenyl C1-C3 alkyl group optionally has one or more substituents selected from Group D”, for example, a benzyl group, a 2-fluorobenzyl group, a 4-chlorobenzyl group, a 4-(trifluoromethyl)benzyl group, and a 2-[4-(trifluoromethyl)phenyl]ethyl group can be mentioned,
  • the term “5- or 6-membered aromatic heterocyclic group” refers to a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group.
  • the 5-membered aromatic heterocyclic group refers to a pyrrolyl group, a furyl group, a thenyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group.
  • a 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms that is a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a 1,2,4-triazolyl group, a 1,2,3-triazolyl group, or a tetrazolyl group is preferable.
  • the 6-membered aromatic heterocyclic group refers to a pyridyl group, a pyridazinyl group, a pyrimidinyl group, or a pyrazinyl group,
  • a group represented by OR 12 refers to a monovalent group in which the oxygen atom at the leftmost has a bonding hand
  • a group represented by NR 11 R 12 refers to a monovalent group in which the nitrogen atom at the leftmost side has a bonding hand
  • a group represented by NR 5 refers to a divalent group in which the nitrogen atom at the leftmost side has a bonding hand.
  • R 3a , R 3b , R 3c , and R 3d are each independently a hydrogen atom, a phenyl group optionally having one or more substituents selected from Group H, a 6-membered aromatic heterocyclic group selected from Group V in which the 6-membered aromatic heterocyclic group optionally has one or more substituents selected from Group H, or a 5-membered aromatic heterocyclic group selected from Group W in which the 5-membered aromatic heterocyclic group optionally has one or more substitutents selected from Group H:
  • R 3x represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms, in which the phenyl group, the 6-membered aromatic heterocycle group, and the 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms each independently optionally has one or more substituents selected from Group H,
  • NR 11 R 12 NR 11 C(O)OR 14 , a hydrogen atom, or a halogen atom.
  • R 2 is at C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms or halogen atoms.
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the friazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom
  • R 4a and R 4c are hydrogen atoms.
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group; and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms or halogen atoms.
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms.
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is CR 4c .
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms, in which the phenyl group, the 6-membered aromatic heterocycle group, and the 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms each independently optionally has one or more substituents selected from Group H,
  • NR 11 R 12 NR 11 C(O)OR 14 , a hydrogen atom, or a halogen atom.
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl groups, a triazolyl group, in which the phenyl group, the pyridyl group the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a , R 4b , and R 4c are hydrogen atoms or halogen atoms.
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally, having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group; and the triazolyl group each independently optionally has one or more substituents from Group H,
  • R 4a , R 4b , and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a , R 4b , and R 4c are hydrogen atoms.
  • R 2 is an ethyl group G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G is CR 3c
  • R 3b and R 3e are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom
  • R 4a , R 4b , and R 4c are hydrogen atoms.
  • R 2 is at C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group-optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a , R 4b , and R 4c are hydrogen atoms or halogen atoms:
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a , R 4b , and R 4c are hydrogen atoms.
  • a 2 is a nitrogen atom
  • a 3 is CR 4b
  • a 4 is CR 4c .
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having-one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4b and R 4c are hydrogen atoms or halogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3e are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4b and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom
  • R 4b and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group and the triazoyl group each independently optionally has one or more substituents selected Group H, an amino group, NR 11 C(O)OR 14 , a hydrogen atom, or a halogen atom, and R 4b and R 4c are hydrogen atoms.
  • a 2 is CR 4a
  • a 3 is a nitrogen atom
  • a 4 is CR 4c .
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a 6-membered aromatic, heterocyclic group, a 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms, in which the phenyl group, the 6-membered aromatic heterocycle group, and the 5-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms each independently optionally has one or more substituents selected from Group H,
  • NR 11 R 12 NR 11 C(O)OR 14 , a hydrogen atom, or a halogen atom.
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group, optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4e are hydrogen atoms or halogen atoms.
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group; and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H, an amino group, NR 11 C(O)OR 14 , a hydrogen atom, or a halogen atom, and R 4a and R 4c are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3e are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom
  • R 4a and R 4 are hydrogen atoms.
  • R 2 is a C1-C6 alkyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group; and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms or halogen atoms.
  • R 2 is an ethyl group
  • R 3a , R 3b , R 3c , and R 3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4c are hydrogen atoms.
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is a nitrogen atom.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H,
  • R 4a and R 4b are hydrogen atoms.
  • R 2 is an ethyl group
  • G 1 and G 4 are CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • R 3b and R 3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom
  • R 4a and R 4b are hydrogen atoms.
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more-halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substitutents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 .
  • R 1 , R 1x , R 1y , and R 1ay are each independently a C1-C5 chain hydrocarbon group having one or more halogen atoms.
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl).
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O) m R 1 , OS(O) 2
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O) m R 1 , OS(O) 2
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O) m R 1 , OS(O) 2
  • T is a group represented by Formula T-1, a group represented by Formula T-2, a group represented by Formula T-3, a group represented by Formula T-4, a group represented by Formula T-5, a group represented by Formula T-6, a group represented by Formula T-7, or a group represented by Formula T-8, and R 1x and R 1y are each independently a C1-C5 alkyl group having three or more fluorine atoms.
  • T is OR 1
  • R 1 is a C1-C5 chain hydrocarbon group having one or more halogen atoms.
  • T is OR 1
  • R 1 is a C1-C5 alkyl group having three or more fluorine atoms
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O) m R
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atom, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having-one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O) m R
  • T is a C1-C10 chain-hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen-atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G a C3-C7 cycloalkyl group-having one or more substituents selected from Group G, OR 1 , S(O
  • T is a C1-C10 chain hydrocarbon group having-one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having-one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group CG a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR 1 , S(O)
  • T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G.
  • OR 1 S(O) m R
  • T is a group represented by Formula T-1, a group represented by Formula T-2, a group represented by Formula T-3, a group represented by Formula T-4, a group represented by Formula T-5, a group represented by Formula T-6a group represented by Formula T-7, or a group represented by Formula T-8, and R 1 , R 1x , and R 1y are each independently a C1-C5 alkyl group having three or more fluorine atoms.
  • T is OR
  • R 1 is a C1-C5 chain hydrocarbon group having one or more halogen atoms.
  • T is OR 1
  • R 1 is a C1-C5 alkyl group having three or more fluorine atoms.
  • G 1 is CR 3a
  • G 2 is CR 3b
  • G 3 is CR 3c
  • G 4 is a nitrogen atom or CR 3d
  • R 3a , R 3b , R 3c , and R 3d are each independently a hydrogen atom, a halogen atom, or a C1-C10 alkyl group having one or more halogen atoms
  • R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms
  • a 2 , A 3 , and A 4 are CH's, or anyone of A 2 , A 3 , and A 4 is a nitrogen atom and the remainder thereof are CH's
  • T is a group selected from Group K
  • a group consisting of a C1-C10 chain hydrocarbon group having one or more halogen atoms such as a difluoromethyl group, a trifluoromethyl group, as 2,2,2-trifluoroethyl group, a perfluoroethyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a perfluorobutyl group, and a perfluoropentyl group;
  • a group represented by OR 1 such as a trifluoromethoxy group, a 1,2,2-tetrafluoroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a perfluoroethoxy group, a 1-methyl-2,2,2-trifluoroethoxy group, a 2,2,3,3-tetrafluoropropoxy group, a 2,2,3,3,3-pentafluoropropoxy group, a perfluoropropoxy group, a 2,2,3,4,4,4-hexafluorobutoxy group, a 2,2,3,3,4,4,4-heptafluorobutoxy group, a perfluorobutoxy group, and a 2,2,3,3,4,4,5,5,5-nonafluoropentyloxy group;
  • a group represented by S(O) m R 1 such as a trifluoromethylsulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, a perfluoroethylsulfariyl group, a 2,2,3,3,3-pentafluoropropylsulfanyl group, a perfluoropropylsulfanyl group, a 2,2,3,3,4,4,4-heptafluorobutylsulfanyl group, a perfluorobutylsulfanyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a perfluoroethylsulfonyl group, a 2,2,3,3,3-pentaluoropropylsulfinyl group, a perfluoropropylsulfonyl group, a 2,2,3,3,4,4,4-
  • OS(O) 2 R 1 such as a trifluoromethylsulfonyloxy group, a perfluoroethylsulfonyloxy group, and a perfluoropropylsulfonyloxy group;
  • CH 2 OR 1 such as a trifluoromethoxymethyl group, a 2,2,2-trifluoroethoxymethyl group, and a perfluoroethoxymethyl group;
  • a group represented by NR 1 R 29 such as a 2,2,2-trifluoroethylamino group, a 2,2,3,3,3-pentafluoropropylamino group, a 2,2,3,3,4,4-heptafluorobutylamino group, an N-methyl-2,2,2-trifluoroethylamino group, an N-methyl-2,2,3,3,3-pentafluoropropylamino group, an N-methyl-2,2,3,3,4,4,4-heptafluorobutylamino group, an N-ethyl-2,2,2-trifluoroethylamino group, an N-ethyl-2,2,3,3,3-pentafluoropropylamino group, and an N-ethyl-2,2,3,3,4,4,4-heptafluorobutylamino group;
  • C(O)R 1 such as a trifluoromethylcarbonyl group, a perfluoroethylcarbonyl group, and a perfluoropropylcarbonyl group;
  • C(O)NR 1 R 29 such as N-methyl-N-(2,2,2-trifluoroethyl)carbamoyl group
  • NR 29 C(O)R 1 such as an N-methyl-trifluoromethylcarbonylamino group
  • N ⁇ CR 1 R 30 such as a 1-ethyl-3,3,3-trifluoropropylideneamino group
  • a group represented by Formula T-1 such as a 3-trifluoromethylphenyl group, a 3,5-bis(trifluoromethyl)phenyl group, a 3-(trifluoromethylsulfanyl)phenyl group, a 3-(trifluoromethylsulfinyl)phenyl group, a 3-(trifluoromethylsulfonyl)phenyl group, a 4-trifluoromethyl-2-pyridyl group, a 4-(trifluoromethylsulfanyl)-2-pyridyl group, a 4-(trifluorontethylsulfinyl)-2-pyridyl group, a 4-(trifluoromethylsulfonyl)-2-pyridyl group, a 5-trifluoromethyl-3-pyridyl group, a 5-(trifluoromethylsulfanyl)-3-pyridyl group, a 5-(trifluoromethylsulfinyl)-3
  • a group represented by Formula T-3 such as a 2,2-difluoro-1,3-benzodioxol-5-yl group;
  • a group represented by Formula T-4 such as a 2,2-difluoro-1,3-benzodioxol-4-yl group
  • a group represented by Formula T-6 such as a 2-oxo-4-(trifluoromethylsulfanyl)-1(2H)-pyridyl group, a 2-oxo-4-(trifluoromethylsulfinyl)-1(2H)-pyridyl group, and a 2-oxo-4-(trifluoromethylsulfonyl)-1(2H)-pyridyl group and
  • a group, represented by Formula T-8 such as a 4-trifluoromethyl-1-imidazolyl group, a 3-trifluoromethyl-1-pyrazolyl group, a 4-trifluoromethyl-1-pyrazolyl group, and a 3-trifluoromethyl-1H-1,2,4-triazol-1-yl group.
  • the compound of the present invention in which Q is a group represented by Formula Q1, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d , R 3a , R 3b , R 3c , and R 3d are each independently a hydrogen atom or a group selected from Group L, R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms, A 2 , A 3 , and A 4 are CH's, or any one of A 2 , A 3 , and A 4 is a nitrogen atom and the remainder thereof are CH's, and T is a group selected from Group K-1.
  • a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group E, such as cyclopropyl group and 1-cyanocyclopropyl group;
  • a phenyl group optionally having one or more substituents selected from Group H, such as a phenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 3,4-difluorophenyl group, a 3,5-difluorophenyl group, a 2,4-difluorophenyl group, a 3,4,5-trifluorophenyl group, a 3,4-dichlorophenyl group, a 3,5-dichlorophenyl group, a 3,5-dichloro-4-fluorophenyl group, a 3-cyanophenyl group, a 4-cyanophenyl group, a 3-trifluoromethylphenyl group, a 4-trifluoromethylphenyl group, a 3-dimethylaminophenyl group, a 4-dimethylaminophenyl group, a
  • a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group H, such as a 1-pyrrolyl group, a 3-fluoro-1-pyrrolyl group, a 3-chloro-1-pyrrolyl group, a 3-bromo-1-pyrrolyl group, a 3-nitro-1-pyrrolyl, group, a 3-amino-1-pyrrolyl group, a 3-methyl-1-pyrrolyl group, a 3-trifluoromethyl-1-pyrrolyl group, a 3-methoxy-1-pyrrolyl group, a 1-imidazolyl group, a 4-fluoro-1-imidazolyl group, a 4-chloroo-1-imidazolyl group, a 4-bromo-1-imidazolyl group, a 4-nitro-1-imidazolyl group, a 4-amino-1-imidazolyl group, a 4-methyl-1-imidazolyl group, a 4-trifluoromethyl
  • OR 12x such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a phenoxy group, a 2-fluorophenoxy group, a 2-pyridyloxy group, and a 3-pyridyloxy group;
  • NR 11 R 12 such as amino group
  • NR 11a R 12a such as 2,2,2-trifluoroethylamino group
  • NR 11 C(O)R 13 such as a cyclopropylcarbonylamino group and an N-methyl-cyclopropylcarbonylamino group
  • C(O)OR 17 such as an ethoxycarbonyl group
  • a group represented by CR 30 ⁇ NOR 17 such as a (hydroxyimino)methyl group, a (methoxyimino)methyl group, an (ethoxyimino)methyl group, a (2,2,2-trifluoroethoxyimino)methyl group, a 1-(hydroxyimino)ethyl group, a 1-(methoxyimino)ethyl group, an 1-(ethoxyimino)ethyl group, a 1-(2,2,2-trifluoroethoxyimino)ethyl group, and an amino(2,2,2-trifluoroethoxyimino)methyl group, a cyano group, a hydrogen atom; and
  • halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom.
  • Q is a group represented by Formula Q2
  • G 1 is CH
  • R 3b is a hydrogen atom, or a C1-C10 alkyl group having one or more halogen atoms
  • R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms
  • a 2 , A 3 and A 4 are, CH's, or any one of A 2 , A 3 , and A 4 is a nitrogen atom and the remainder thereof are CH's
  • T is a group selected from Group K.
  • the compound of the present invention in which Q is a group represented by Formula Q3, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3b , G 4 is CR 3d , R 3a , R 3b , R 3c and R 3d are each independently a hydrogen atom, or a C1-C10 alkyl group having one or more halogen atoms, R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms, A 1 is NR 5 or a sulfur atom, R 5 is a C1-C6 alkyl group optionally having one or more halogen atoms, A 2 , A 3 , and A 4 are CH's, or any one of A 2 , A 3 , and A 4 is a nitrogen atom and the remainder thereof are CH's, and T is selected from Group K.
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is CR 4c
  • Q is a group represented by Formula Q1
  • R 2 is an ethyl group
  • G 1 and G 4 are nitrogen atoms or CH's
  • G 2 is R 3b
  • G 3 is R 3c
  • any one of R 3b and R 3c is a hydrogen atom and the other is a C1-C6 alkyl group optionally having one or more halogen atoms, a hydrogen atom, or a halogen atom
  • R 4a , R 4b , and R 4c are hydrogen atoms
  • T is a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 3b , R 3c , and R 3d are each independently a hydrogen atom, a halogen atom, or a C1-C10 alkyl group having one or more halogen atoms
  • R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms
  • a 2 , A 3 , and A 4 are CH's, or one of A 2 , A 3 , and A 4 is a nitrogen atom and the remainder thereof are CH's
  • T is a group selected from Group K.
  • G 1 is a nitrogen atom
  • G 2 is CR 3b
  • G 3 is CR 3c
  • G 4 is CR 3d
  • R 3b , R 3c , and R 3d are each independently a hydrogen atom or a group selected from Group L
  • R 2 is a C1-C6 alkyl group optionally having one or more halogen atoms
  • a 2 , A 3 , and A 4 are CH's, or any one of A 2 , A 3 , and A 4 is a nitrogen atom and the remainder thereof are CH's
  • T is a group selected from Group K-1.
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is CR 4c
  • Q is a group represented by Formula Q1
  • R 2 is an ethyl group
  • G 1 is a nitrogen atom
  • G 2 is CR 3b
  • G 3 is CR 3c
  • G 4 is CH
  • any one of R 3b and R 3c is a hydrogen atom and the other is a C1-C6 alkyl group optionally having one or more halogen atoms, a hydrogen atom, or a halogen atom
  • R 4a , R 4b , and R 4c are hydrogen atoms
  • T is a C1-C6 alkyl group optionally having one or more halogen atoms.
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is a nitrogen atom
  • Q is a group represented by Formula Q1
  • R 2 is an ethyl group
  • G 1 is a nitrogen atom
  • G 2 is CR 3b
  • G 3 is CR 3c
  • G 4 is CH
  • any one of R 3b and R 3c is a hydrogen atom and the other is a C1-C6 alkyl group optionally having one or more halogen atoms, a hydrogen atom, or a halogen atom
  • R 4a and R 4b are hydrogen atoms
  • T is a C1-C6 alkyl group optionally having one or more halogen atoms.
  • a 2 is a nitrogen atom
  • a 3 is CR 4b
  • a 4 is CR 4c
  • Q is a group represented by Formula Q1
  • R 2 is an ethyl group
  • G 1 and G 4 are nitrogen atoms or CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • any one of R 3b and R 3c is a hydrogen atom and the other is a C1-C6 alkyl group optionally having one or more halogen atoms, a hydrogen atom, or a halogen atom
  • R 4b and R 4c are hydrogen atoms
  • T is a C1-C6 alkyl group optionally having one or more-halogen atoms.
  • a 2 is CR 4a
  • a 3 is CR 4b
  • a 4 is a nitrogen atom
  • Q is a group represented by Formula Q1
  • R 2 is an ethyl group
  • G 1 and G 4 are nitrogen atoms or CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • anyone of R 3b and R 3c is a hydrogen atom
  • the other is a C1-C6 alkyl group optionally having one or more halogen atoms
  • R 4a and R 4b are hydrogen atoms
  • T is a C1-C6 alkyl group optionally having one or more halogen atoms.
  • a 2 is CR 4a
  • a 3 is a nitrogen atom
  • a 4 is CR 4c
  • Q is a group represented by Formula Q1
  • R 2 is an ethyl group
  • G 1 and G 4 are nitrogen atoms or CH's
  • G 2 is CR 3b
  • G 3 is CR 3c
  • any one of R 3b and R 3e is a hydrogen atom and the other is a C1-C6 alkyl group optionally having one or more halogen atoms, a hydrogen atom, or a halogen atom
  • R 4a and R 4 are hydrogen atoms
  • T is a C1-C6 alkyl group optionally having one or more halogen atoms.
  • a compound represented by Formula (II-1-b) (hereinafter referred to as Compound (II-1-b)) or a compound represented by Formula (II-1-c) (hereinafter referred to as Compound (II-1-c)) can be produced by oxidizing a compound represented by Formula (II-1-a) (hereinafter referred to as Compound (II-1-a)).
  • a reaction is usually carried out in a solvent.
  • a solvent for example halogenated hydrocarbons (hereinafter referred to as halogenated hydrocarbons) such as dichloromethane and chloroform, nitriles (hereinafter referred to as nitriles) such as acetonitrile, alcohols (hereinafter referred to as alcohols) such as methanol and ethanol, acetic acid, water, and mixtures thereof can be mentioned.
  • oxidizing agent used in the reaction for example, sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide can be mentioned.
  • a base or a catalyst may be added as necessary.
  • sodium carbonate As the base used in the reaction, sodium carbonate can be mentioned.
  • tungstic acid and sodium tungstate can be mentioned.
  • the oxidizing agent is used in an amount of usually 1 to 1.2 mol.
  • the base is used in an amount of usually 0.01 to 1 mol, and the catalyst is used in an amount of usually 0.01 to 0.5 mol, with respect to 1 mol of Compound (II-1-a).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 80° C.
  • a reaction time is usually in a range of 0.1 to 12 hours.
  • a reaction is usually carried out in a solvent.
  • a solvent used in the reaction for example, halogenated hydrocarbons, nitriles alcohols, acetic acid, water, and mixtures thereof can be mentioned.
  • an oxidizing agent used in the reaction for example, mCPBA, and hydrogen peroxide can be mentioned.
  • a base or a catalyst may be added as necessary.
  • sodium carbonate As the base used in the reaction, sodium carbonate can be mentioned.
  • sodium tungstate As the catalyst used in the reaction, for example, sodium tungstate can be mentioned.
  • the oxidizing agent is used in an amount of usually 1 to 2 mol
  • the base is in an amount of usually 0.01 to 0.1 mol
  • the catalyst is used in an amount of usually 0.01 to 0.5 mol, with respect to 1 mol of Compound (II-1-b).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 120° C.
  • a reaction time is usually in a range of 0.1 to 12 hours.
  • Compound (II-1-c) can be produced in a one-step reaction (one pot) by reacting Compound (II-1-a) with anoxidizing agent.
  • the reaction can be carried out according to the method for producing Compound (II-1-c) from Compound (II-1-b) by using an oxidizing, agent in an amount of usually 2 to 5 mol with respect to 1 mol of Compound (II-1-a).
  • a compound represented by Formula (II-2-b) and a compound represented by Formula (II-2-c) can be produced by oxidizing a compound represented by Formula (II-2-a).
  • a compound represented by Formula (II-3-b) and a compound represented by Formula (II-3-c) can be produced by oxidizing a compound represented by Formula ((II-3-a).
  • Compound (II-1-a) can be produced according to the following scheme.
  • X b represents a chlorine atom, a bromine atom, or an iodine atom, and the other symbols have the same meanings as defined above.
  • Compound (M-2) can be produced by reacting a compound represented by Formula (M-1) (hereinafter referred to as Compound (M-1)) with a compound represented by Formula (R-1) (hereinafter referred to as Compound (R-1)).
  • the reaction is usually carried out in a solvent.
  • ethers such as tetrahydrofuran (hereinafter referred to as THF), 1,4-dioxane, ethylene glycol dimethyl ether (hereinafter referred to as DME), methyl tert-butyl ether (hereinafter referred to as MTBE), aromatic hydrocarbons (hereinafter referred to as aromatic hydrocarbons) such as toluene and xylene, an aprotic polar solvents (hereinafter referred to as aprotic polar solvents) such as dimethylformamide (hereinafter, referred to as DMF), N-methylpyrrolidone and dimethylsulfoxide (hereinafter referred to as DMSO), alcohols, nitriles, water, and mixtures thereof can be mentioned.
  • DMF dimethylformamide
  • DMSO N-methylpyrrolidone and dimethylsulfoxide
  • a base can be used as necessary.
  • organic bases such as: triethylamine, diisopropylethylamine, pyridine, and 4-(dimethylamino) pyridine
  • alkali metal carbonates hereinafter referred to as alkali metal carbonates
  • sodium carbonate and potassium carbonate can be mentioned.
  • Compound (R-1) is used in an, amount of usually 1 to 10 mol and the base is used in an amount of usually 0.1 to 5 mol, with respect to 1 mol of Compound (M-1).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 48 hours.
  • Compound (R-1) can be a commercially available compound or can be produced using a known method.
  • Compound (M-3) can be produced by reacting Compound (M-2) with a halogenating agent.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures thereof can be mentioned.
  • halogenating agent chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, and the like can be mentioned.
  • the halogenating agent is used in an amount of usually 1 to 20 mol with respect to 1 mol of Compound (M-2).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 72 hours.
  • Compound (II-1-a) can be produced by reacting Compound (M-2) with a compound represented by Formula (R-2) (hereinafter referred to as Compound (R-2)) and a halogenating agent.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures thereof can be mentioned.
  • halogenating agent chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, and the like can be mentioned.
  • Compound (R-2) is used in an amount of usually 1 to 20 mol with respect to 1 mol of Compound (M-2).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 72 hours.
  • Compound (II-1-a) can be obtained.
  • Compound (R-2) can be a commercially available compound or can be produced using a known method.
  • Compound (II-1-a) can also be produced by reacting Compound (M-3) with Compound (R-2) in the presence of a metal catalyst and a base.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, aid mixtures thereof can be mentioned.
  • a palladium catalyst such as tetrakis(triphenylphospliine)-palladium (0), 1,1′-bis(diphenylphosphino) ferrocene palladium (II) dichloride, tris(dibenzylideneacetone) dipalladium (0), and palladium (II) acetate
  • a nickel catalyst such as bis(cyclooctadiene) nickel (0) and nickel (II) chloride
  • a copper catalyst such as copper (I) iodide and copper (I) chloride, and the like can be mentioned.
  • alkali metal hydrides such as sodium hydride, alkali metal carbonates, and organic bases can be mentioned.
  • a ligand can also be used.
  • the ligand used in the reaction triphenylphosphine, xantphos, 2,2′-bis(diphenylphiosphino)-1,1′-binaphtlhyl, 1,1′-bis(diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2′,4′,6′-triisopropyibiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino) ethane, 2,2′-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, and the like can be mentioned.
  • Compound (R-2) is used in an amount of usually 1 to 20 mol
  • the metal catalyst is used in an amount of usually 0.01 to 0.5 mol
  • the ligand is used in an amount of usually 0.01 to 1 mol
  • the base is used in an amount of usually 0.1 to 5 mol, with respect to 1 mol of Compound (M-3).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 72 hours.
  • Compound (II-1-a) can be produced by reacting Compound (R-1) with a compound represented by Formula (M-4) (hereinafter referred to as Compound (M-4)),
  • the reaction can be carried out according to the method for producing Compound (M-2) from Compound (M-1) in the production method 4.
  • Compound (II-2-a) A compound represented by Formula (II-2-a) (hereinafter referred to as Compound (II-2-a)) can be produced according to the following scheme.
  • a compound represented by Formula (M-5) (hereinafter referred to as Compound (M-5)) can be produced by reacting Compound (M-1) with a compound represented by Formula (R-4) (hereinafter referred to as Compound (R-4)).
  • Compound (II-2-a) can be produced by reacting Compound (M-5) with Compound (R-2) and a halogenating agent.
  • a compound represented by Formula (M-6) (hereinafter referred to as Compound (M-6)) can be produced by reacting Compound (M-5) with a halogenating agent.
  • Compound (II-2-a) can also be produced by reacting Compound (M-6) with Compound (R-2) in the presence of a metal catalyst and a base.
  • Compound (R-4) can be a commercially available product or can be produced using a known production method.
  • Compound (II-2-a) can be produced by reacting Compound (R-4) with Compound (M-4).
  • the reaction can be carried out according to the method for producing Compound (M-2), from Compound (M-1) in the production method 4.
  • a compound represented by Formula (II-3-a) (hereinafter referred to as Compound (II-3-a)) can be produced according to the following scheme.
  • M represents a 9-borabicyclo[3.3.1]nonan-9-yl group, a borono group, a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, a tributylstannyl group, ZnCl, MgCl, or MgBr, and the other symbols have the same meanings as defined above.
  • Compound (M-10) can be produced by reacting a compound represented by Formula (M-8) (hereinafter referred to as Compound (M-8)) with a compound represented by Formula (M-9) (hereinafter referred to as Compound (M-9)) in the presence of a metal catalyst.
  • the reaction is usually carried out in a solvent.
  • a solvent used in the reaction for example, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures thereof can be mentioned.
  • a metal catalyst used in the reaction a palladium catalyst such as tetrakis(triphenyphosphine) palladium (0), 1,1′-bis(diphenylphosphino) ferrocene palladium (II) dichloride, tris(dibenzylideneacetone) dipalladium (0), and palladium (II) acetate, a nickel catalyst such as bis(cyclooctadiene) nickel (0) and nickel (II) chloride, a copper catalyst such as copper (1) iodide and copper (1) chloride, and the like can be mentioned.
  • a ligand, a base, or an inorganic halide may be added as necessary.
  • alkali metal hydrides for example, alkali metal hydrides, alkali metal carbonates, and organic bases can be mentioned.
  • alkali metal fluorides such as potassium fluoride and sodium fluoride
  • alkali metal chlorides such as lithium chloride and sodium chloride
  • Compound (M-9) is used in an amount of usually 1 to 10 mol
  • the metal catalyst is used in an amount of usually 0.01 to 0.5 mol
  • the ligand is used in an amount of usually 0.01 to 1 mol
  • the base is used in an amount of usually 0.1 to 5 mol
  • the inorganic halide is used in an amount of usually 0.1 to 5 mol, with respect to 1 mol of Compound (M-8).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • Compound (M-11) can be produced by reacting Compound (M-10) with a halogenating, agent. The reaction can be carried out according to the method for producing Compound (M-3) from Compound (M-2) in the production method 4.
  • Compound (II-3-a) can be produced by reacting Compound (M-10) with Compound (R-2) and a halogenating agent.
  • the reaction can be carried out according to the method for producing Compound (II-1-a) from Compound (M-2) in the production method 4.
  • Compound (II-3-a) can also be produced by reacting Compound (M-11) with Compound (R-2) in the presence of a metal catalyst and a base. The reaction can also be carried out according to the method for producing Compound (II-1-a) from Compound (M-3) in the production method 4.
  • Compound (M-8) can be a commercially available compound, or can be produced using a known production method or a method described in reference production methods 12 to 21.
  • Compound (M-9) is a commercially-available compound or is known.
  • RP represents a methyl group or an ethyl group, and the other symbols have the same meanings as defined above.
  • a compound represented by Formula (M-14)(hereinafter referred to as Compound-(M-14)) can be produced from a compound represented by Formula (M-12) (hereinafter referred to as Compound (M-12)).
  • a reaction can be carried out, for example, according to the method described in Journal of Medicinal Chemistry, 56, 3980 (2013).
  • a compound represented by Formula (M-15) (hereinafter referred to as Compound (M-15)) can be produced by reacting Compound (M-14) with methylmagnesium chloride.
  • the reaction can be carried out, for example, according to the method described in PCT International Publication No. WO 2008/116665.
  • Compound (M-1) can be produced by reacting Compound (M-15) with a halogenating agent.
  • the reaction can be carried out according to the method described in PCT International Publication No WO 2013/191113,
  • a compound represented by Formula (M-16) (hereinafter referred to as Compound (M-16)) can be produced by reacting Compound (M-1) with Compound (R-2) in the presence of a base.
  • the reaction can be carried out according to the method described in Tetrahedron Letters, 64, 7419 (2008).
  • Compound (M-4) can be produced by reacting Compound (M-16) with a halogenating agent.
  • the reaction can be carried out according to the method described in PCT International Publication No. WO 2013/191113.
  • a compound represented by Formula. (M-12a) (hereinafter referred to as Compound (M-12a)) can be produced by reacting a compound represented by Formula (M-18a) (hereinafter, referred to as Compound (M-18a)) with a compound represented by Formula (R-5) (hereinafter referred to as Compound (R-5)) in the presence of a base.
  • X a represents a fluorine atom or a chlorine atom
  • T 2 represents OR 1 , NR 1 R 29 , a group represented by Formula T-5, a group represented by Formula T-6, a group represented by Formula T-7, or a group represented by Formula T-8, and the other symbols have the same meanings as defined above.
  • the reaction is usually carried out in, a solvent.
  • a solvent for example ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures thereof can be mentioned.
  • alkali metal carbonates or alkali metal hydrides can be mentioned.
  • Compound (R-5) is used in an amount of usually 1 to 2 mol and the base is used in an amount of usually 1 to 10 mol, with respect to 1 mol of Compound (M-18a).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 150° C.
  • a reaction time is usually in a range of 0.5 to 24 hours.
  • Compound (R-5) and Compound (M-1.8a) can be commercially available compounds, or can be produced using known methods.
  • the compound represented by Formula (M-12b) can be prepared by reacting a compound represented by Formula (M-18b), (hereinafter referred to as Compound (M-18b)) and a compound represented by Formula (R-6) (hereinafter referred to as Compound (R-6)).
  • T 3 is a group represented by Formula T-1, a group represented by Formula T-2, a group represented by Formula T-3, a group represented by Formula T-4, a group represented by Formula T-9, a group represented by Formula T-10, a group represented by Formula T-11, or a group represented by Formula T-12, and the other symbols have the same meanings as defined above.
  • the reaction can be carried out according to the method for producing Compound (M-10) as described in the production method 8.
  • Compound (R-6) and Compound (M-18b) can be commercially available compounds or can be produced using known methods.
  • a compound represented by Formula (M-12c) can be produced by reacting a compound represented by Formula (M-18c) (hereinafter referred to as Compound (M-18c)) with a compound represented by Formula (R-7) (hereinafter referred to as Compound (R-7)).
  • reaction can be carried out according to the method described in PCT International Publication No. WO 2016/121969:
  • Compound (R-7) and Compound (M-18c) can be commercially available compounds or can be produced using known methods.
  • a compound represented by Formula (M-12d) (hereinafter referred to as Compound (M-12d)) can be produced by reacting Compound (M-18b) with a compound represented by Formula (R-8) (hereinafter referred to as Compound (R-8)) in the presence of copper.
  • T 4 represents a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G. or a C3-C7 cycloalkyl group having one or more substituents selected from Group G, and the other symbols have the same meanings as defined above.
  • Compound (R-8) can be a commercially available compound or can be produced according to a known method.
  • the reaction is usually carried out in a solvent.
  • the solvent used in the reaction for example, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof can be mentioned.
  • Compound (R-8) is used in an amount of usually 1 to 10 mol and the copper is used in an amount of usually 1 to 10 mol, with respect to 1 mol of Compound (M-18b).
  • a reaction temperature is usually in a range of 40° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • a compound represented by Formula (M-12e) (hereafter referred to as Compound (M-12e)) can be produced by reacting a compound represented by Formula (M-18d) (hereinafter referred to as Compound (M-18d)) with a compound represented by Formula (R-9) (hereinafter referred to as Compound (R-9)),
  • Compound (M-18d) and Compound (R-9) can be commercially available compounds or can be produced according to known methods.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, ethers, halogenated hydrocarbons, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof can be mentioned.
  • abase may be added as necessary.
  • organic bases can be mentioned.
  • Compound (R-9) is, used in an amount of usually 1 to 10 mol and the base is used in an amount of usually 0.1 to 10 mol, with respect to 1 mol of Compound (M-18d).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 120° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • a compound represented by Formula (M-12f) (hereinafter referred to as Compound (M-12f)) can be produced by reacting Compound. (M-18b) with a compound represented by Formula (R-10) (hereinafter referred to as Compound (R-10)) in the presence of a base.
  • R 40 represents a methoxy group, an ethoxy group, a phenoxy group; or N(CH 3 )OCH 3 , and the other symbols have the same meanings as defined above.
  • Compound (R-10) can be a commercially available compound or can be produced according to a known method.
  • the reaction is usually carried out in a solvent.
  • ethers, and aromatic hydrocarbons can be mentioned.
  • butyllithium lithium diisopropylamide, lithium tetramethylpiperidide, lithium bis(trimethylsilyl) amide, and the like can be mentioned.
  • Compound (R-10) is used in an amount of usually 1 to 10 mol and the base is usually used in an amount of 1.0 to 2.0 mol, with respect to 1 mol of Compound (M-18b).
  • a reaction temperature is usually in a range of ⁇ 100° C. to 60° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • a compound represented by Formula (M-12 g) (hereinafter referred to as Compound (M-12 g)) can be produced by reacting a compound represented by Formula (M-18e)(hereinafter referred to as Compound (M-18e)) with a compound represented by Formula (R-11) (hereinafter referred to as Compound (R-11)) in the presence of a condensing agent.
  • Compound (R-11) and Compound (M-18e) can be commercially available compounds or can be produced according to known methods.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, ethers, aliphatic halogenated hydrocarbons, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof can be mentioned.
  • 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and the like can be mentioned.
  • a base may be added as necessary.
  • organic bases can be mentioned.
  • Compound (R-11) is used in an amount of usually 1 to 10 mol
  • the condensing agent is used in an amount of usually 1 to 5, mol
  • the base is used in an amount of usually 0.1 to 10 mol, with respect to 1 mol of Compound (M-18e).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 120° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • a compound represented by Formula (M-12h) (hereinafter referred to as Compound (M-12h)) can be produced by reacting a compound represented by Formula (M-18f) (hereinafter referred to as Compound (M-18f) with a compound represented by Formula (R-12) (hereinafter referred to as Compound (R-12)).
  • Compound (R-12) and Compound (M-18f) can be commercially available compounds or can be produced according to known methods.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, ethers, aliphatic halogenated hydrocarbons, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof can be mentioned.
  • an acid may be added as necessary.
  • the acid p-toluenesulfonic acid and camphorsulfonic acid can be mentioned.
  • Compound (R-12) is used in an amount of usually 1 to 10 mol and the acid is used in an amount of usually 0.1 to 10 mol, with respect to 1 mol of Compound (M-18f).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 180° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • a compound represented by Formula (M-12i) (hereinafter referred to as Compound (M-12i)) can be produced by reacting a compound represented by Formula (M-18 g) (hereinafter referred to as Compound (M-18 g)) with a compound represented by Formula (R-13) (hereinafter referred to as Compound (R-13) in the presence of a base.
  • Compound (R-13) and Compound (M-18 g) can be commercially available compounds or can be produced according to known methods.
  • the reaction is usually carried out in a solvent.
  • a solvent used in the reaction, ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof tan be mentioned.
  • Compound (R-13) is used in an amount of usually 1 to 10 mol and the base is used in an amount of usually 0.1 to 5 mol, with respect to 1 mol of Compound (M-18 g):
  • a reaction temperature is usually in a range of ⁇ 20° C. to 120° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • a compound represented by Formula (M-12j) (hereinafter referred to as Compound (M-12j)), a compound represented by Formula (M-12j-1) (hereinafter referred to as Compound (M-12j-1)), and a compound represented by Formula (M-12j-2) (hereinafter referred to as Compound (M-12j-2)) can be produced according to the following methods.
  • Compound (M-20) can be produced by reacting Compound (M-18b) with thiobenzoic acid in the presence of a copper catalyst and a base.
  • the reaction is usually carried out in a solvent.
  • a solvent for example, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures thereof can be mentioned.
  • copper catalyst used in the reaction copper chloride, copper bromide, copper iodide, and the like can be mentioned.
  • alkali metal hydrides As the base used in the reaction, alkali metal hydrides, alkali metal carbonates, and organic bases can be mentioned.
  • a ligand may be added as necessary.
  • the thiobenzoic acid is used in an amount of usually 1 to 1.0 mol
  • the copper catalyst is used in an amount of usually 0.01 to 0.5 mol
  • the ligand is used in an amount of usually 0.01 to 1 mol
  • the base is used in an amount of usually 0.1 to 5 mol, with respect to 1 mol of Compound (M-18b).
  • a reaction temperature is usually in a range of ⁇ 20° C. to 200° C.
  • a reaction time is usually in a range of 0.1 to 24 hours.
  • Compound (M-21) can be produced for example, according to the method described in PCT International Publication No. WO 2011/068171 or the method described in Journal of Organic Chemistry, 1978, 43(6), pp. 1190 to 192.
  • Compound (M-12j) can be produced according to the method described in the reference production method 10, using Compound (M-21) in place, of Compound (M-18 g).
  • Compound (M-12j-1) can be produced according to the method described in the production method 1, using Compound (M-12j) in place of Compound (II-1-a).
  • Compound (M-12j-2) can be produced according to the method described in Production Method 1, using Compound (M-12j-1) in place of Compound (II-1-b).
  • a compound represented by Formula (M-8a) (hereinafter referred to as Compound (M-8a)) can be produced by reacting a compound represented by Formula (M-19a) (hereinafter referred to as Compound (M-19a)) with Compound (R-5):
  • the reaction can be carried out according to the method described in the reference production method 2.
  • Compound (M-19a) can be a commercially available compound or can be produced using a known method.
  • a compound represented by Formula (M-8b) can be produced by reacting a compound represented by Formula (M-19b) (hereinafter referred to as Compound (M-19b) with Compound (R-6).
  • the reaction can be carried out according to the method described in the reference-production method 3.
  • Compound (M-19b) can be a commercially available compound or can be produced using, a known method.
  • a compound represented by Formula (M-8c) (hereinafter referred to as Compound (M-8c)) can be produced by reacting a compound represented by Formula (M-19c) (hereinafter referred to as Compound (M-19c)) with Compound (R-7).
  • the reaction can be carried out according to the method described in the reference production method 4.
  • Compound (M-19c) can be a commercially available compound or can be produced using a known method.
  • a compound represented by formula (M-8d) (hereinafter referred to as Compound (M-8d)) can be produced by reacting Compound (M-19b) with Compound (R-8).
  • the reaction can be carried out according to the method described in the reference production, method 5.
  • a compound represented by Formula (M-8e) (hereinafter referred to as Compound (M-8e)) can be produced by reacting a compound represented by Formula (M-19d) (hereinafter referred to as Compound (M-19 d)) with Compound (R-9).
  • reaction can be carried out according to the method described in the reference production method 6,
  • Compound (M-19d) can be a commercially available compound or can be produced using a known method.
  • a compound represented by Formula (M-8f) (hereinafter referred to as Compound (M-8f)) can be produced by reacting Compound (M-19b) with Compound (R-10).
  • the reaction can be carried out according to the method described in the reference production method 7.
  • a compound represented by Formula (M-8 g) (hereinafter referred to as Compound (M-8 g)) can be produced by reacting a compound represented by Formula (M-19e) (hereinafter referred to as Compound (M-19e)) with Compound (R-11).
  • the reaction can be carried out according to the method described in the reference production method 8.
  • Compound (M-19e) can be a commercially available compound or can be produced using a known method.
  • a compound represented by Formula (M-8h) (hereinafter referred to as Compound (M-8h)) can be produced by reacting a compound represented by Formula (M-19f) (hereinafter referred to as Compound (M-19f)) with Compound (R-12).
  • reaction can be carried out according to the method described in the reference production, method 9.
  • Compound (M-19f) can be a commercially available compound or can be produced using a known method.
  • a compound represented by Formula (M-8i) (hereinafter referred to as Compound(M-8i)) can be produced by reacting a compound represented by Formula (M-19 g) (hereinafter referred to as Compound (M-19 g)) with Compound (R-13),
  • the reaction can be carried out according to the method described in reference production method 10.
  • Compound (M-19 g) can be a commercially available compound or can be produced using a known method.
  • a compound represented by formula (M-8j) (hereafter referred to as Compound (M-8j)), a compound represented by Formula (M-8j-1). (hereinafter referred to as Compound (M-8j-1), and a compound represented by Formula (M-8j-2) (hereinafter referred to as Compound (M-8j-2) can be produced according to the following methods.
  • the reactions can be carried out according to the methods described in reference production method 1.1.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • i-Pr represents an isopropyl group
  • c-Pr represents a cyclopropyl group
  • 1-CN-c-Pr represents a 1-cyanocyclopropyl group
  • Ph represents a phenyl group
  • Py2 represents a 2-pyridyl group
  • Py3 represents a 3-pyridyl group
  • Py4 represents a 4-pyridyl group
  • the substituent is specified before the symbol together with a substitution position.
  • 4-C F-Py2 represents a 4-(trifluoromethyl)-2-pyridyl group and 3,5-(CF 3 ) 2 -Ph represents a 3,5-bis(trifluromethyl)phenyl group.
  • a compound represented by Formula (L-1) (hereinafter referred to as Compound (L-1)) in which R 3b and R 3c are hydrogen atoms and T is any one of the substituents, described in Tables 1 to 6 (hereinafter referred to as Compound Group SX1).
  • a compound represented by Formula (L-2) (hereinafter referred to as Compound (L-2)) in which R 3b and R 3c are hydrogen atoms and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX6).
  • a compound represented by Formula (L-3) (hereinafter referred to as Compound (L-3)) in which R 3b and R 3c are hydrogen atoms and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX11).
  • Compound (L-3) in which R 3b is a hydrogen atom, R 3 is a chlorine atom, aid T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX14).
  • a compound represented by Formula (L-4) (hereinafter referred to as Compound (L-4)) in which R 3b and R 3c are hydrogen atoms and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX16).
  • a compound represented by Formula (L-5) (hereinafter referred to as Compound (L-5)) in WHICH R 3b and R 3C are hydrogen atoms and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX21).
  • a compound represented by Formula (L-6) (hereinafter referred to as Compound (L-6)) in which R 3b and R 3c are hydrogen atoms and T is any one of the substituents described in Tables 1 to 6′(hereinafter referred to as Compound Group SX26).
  • a compound represented by Formula (L-7) (hereinafter referred to as Compound (L-7)) in which R 3b and R 3c are hydrogen atoms, and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX3).
  • a compound represented by Formula (L-8) (hereinafter referred to as Compound (L-8)) in which R 3b and R 3c are hydrogen atoms and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX36).
  • a compound represented by Formula (L-9) (hereinafter referred to as Compound (L-9)) in which G 1 is CH, R 3b is a hydrogen atom, and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX41).
  • Compound (L-9) in which G 1 is CH, R 3b is a trifluoromethyl group, and T is any one of the substituents described in Tables 1 to 6 hereinafter referred to as Compound Group SX42.
  • a compound represented by Formula (L-10) (hereinafter referred to as Compound (L-10)) in which G 1 is CH, R 3b is a hydrogen atom and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX45).
  • Compound (L-10) in which G 1 is a nitrogen atom, R 3b is a hydrogen atom and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX47).
  • a compound represented by Formula (L-11) (hereinafter referred to as Compound (L-11)) in which G 1 is CH, R 3b is a hydrogen atom, and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX49).
  • Compound (L-11) in which G 1 is CH, R 3b is a trifluoromethyl group, and T is any one of the substituents described in Tables 1 to 6 hereinafter referred to as Compound Group SX50.
  • a compound represented by Formula (L-12) (hereinafter referred to as Compound (L-12)) in which G is CH, R 3b is a hydrogen atoms and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX53).
  • a compound represented by Formula (L-13) (hereinafter referred to as Compound (L-13)) in which A 1 is N—CH 3 and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX57).
  • Compound (L-13) in which A 1 is a sulfur atom and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX58).
  • a compound represented by Formula (L-14) (hereinafter referred to as Compound (L-14)) in which A 1 is N—CH 3 and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX59).
  • Compound (L-14) in which A 1 is a sulfur atom and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX60).
  • a compound represented by Formula (L-15) (hereinafter referred to as Compound (L-15)) in which A 1 is N—CH 3 and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX61).
  • Compound (L-15) in which A 1 is a sulfur atom and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX62).
  • a compound represented by Formula (L-16) (hereinafter referred to as Compound (L-16)) in which A 1 , is N—CH 3 and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX63),
  • Compound (L-16) in which A 1 is a sulfur atom and T is any one of the substituents described in Tables 1 to 6 (hereinafter referred to as Compound Group SX64).
  • a compound represented by Formula (L-17) (hereinafter referred to as Compound (L-17)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX65).
  • a compound represented by Formula (L-18) (hereinafter referred to as Compound (L-48)) in which G 4 is CH, R 3b is a hydrogen atom and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX69).
  • Compound (L-18) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 hereinafter referred to as Compound Group SX70.
  • Compound (L-19) A compound represented by Formula (L-19) (hereinafter referred to as Compound (L-19)) in which G 4 is CH, R A is a hydrogen atom, and R 3e is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX73).
  • a compound represented by Formula (L-20) (hereinafter referred to as Compound (L-20)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX77).
  • Compound (L-20) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX80).
  • a compound represented by Formula (L-21) (hereinafter referred to as Compound (L-21)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3e is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX81).
  • Compound (L-21) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX84).
  • a compound represented by Formula (L-22) (hereinafter referred to as Compound (L-22)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX85):
  • a compound-represented by Formula (L-23) (hereinafter referred to as Compound (L-23)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX89).
  • Compound (L-23) in which G 4 is a nitrogen atom, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX91).
  • Compound (L-24) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 1.5 (hereinafter referred to as Compound Group SX94).
  • a compound represented by Formula (L-25) (hereinafter referred to as Compound (L-25)) in which G 4 is CH, R 3b is a hydrogen atom; and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX97).
  • a compound represented by Formula (L-26) (hereinafter, referred to as Compound (L-26)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX101).
  • a compound represented by Formula (L-27) (hereinafter referred to as Compound (L-27)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX105).
  • Compound (L-27) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX106).
  • a compound represented by Formula (L-28) (hereinafter referred to as Compound (L-28)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX109).
  • Compound (L-28) in which, G 4 is CH, R 3c is a hydrogen atom, and R 3b is anyone of the substituents described in Tables 7 to 1:5 hereinafter referred to as Compound Group SX110).
  • a compound represented by Formula (L-29) (hereinafter referred to as Compound (L-29)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX113).
  • Compound (L-29) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables, 7 to 15 (hereinafter referred to as Compound Group SX114).
  • a compound represented by Formula (L-30) (hereinafter referred to as Compound (L-30)) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX117),
  • a compound represented by Formula (L-31) (hereinafter referred to as Compound (L-31)) in which G is CH, R 36 is a hydrogen atom, and R 3c is anyone of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX121).
  • Compound (L-31) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX122).
  • Compound (L-31) in which G 4 is a nitrogen atom, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX123):
  • Compound (L-31) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX124).
  • a compound represented by Formula (L-32) (hereinafter referred to as Compound (L-32)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX125):
  • Compound (L-32) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX126).
  • Compound (L-32) in which G 4 is a nitrogen atom, R 3b is a hydrogen atom and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX127):
  • Compound (L-32) in which G 4 is a nitrogen atom R 3c is a hydrogen atom and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX128).
  • a compound represented by Formula, (L-33) (hereinafter referred to as Compound (L-33)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX129).
  • Compound (L-33) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX130).
  • Compound (L-33) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX132).
  • a compound represented by Formula (L-34) (hereinafter referred to as Compound (L-34)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter, referred to as Compound Group SX133).
  • Compound (L-34) in which G 4 is CH, R 3e is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 hereinafter referred to as Compound Group SX134.
  • Compound (L-34) in which G is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is anyone of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX136).
  • a compound represented by Formula (L-35) (hereinafter referred to as Compound (L-35)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX137).
  • Compound (L-35) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX138).
  • Compound (L-35) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents-described in Tables 7 tot 15 (hereinafter referred to as Compound Group SX140).
  • a compound represented by Formula (L-36) (hereinafter referred to as Compound (L-36)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX141).
  • Compound (L-36) in which G 4 is CH R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX142).
  • a compound represented by Formula (L-37) (hereinafter referred to as Compound (L-37)) in which G 4 is CH, R 3b is a hydrogen atom and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX145).
  • a compound represented by Formula (L-38) (hereinafter referred to as Compound (L-38)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX149).
  • a compound represented by Formula (L-39) (hereinafter referred to as Compound (L-39)) in which G 4 is CH, R 3b is a hydrogen atom and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX153).
  • Compound (L-39) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX154).
  • a compound represented by Formula (L-40) (hereinafter referred to as Compound (L-40)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX157).
  • Compound (L-40) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX158).
  • Compound (L-40) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX160).
  • a compound represented by Formula (L-41) (hereafter referred to as Compound (L-41)) in which G 4 is CH, R 3b is a hydrogen atom and R 3c is any one of the substituents described in Tables 7 to 15 (hereafter referred to as Compound Group SX161).
  • Compound (L-41) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 hereinafter referred to as Compound Group SX162.
  • Compound (L-41) in which G 4 is a nitrogen atom, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX164).
  • a compound represented by Formula (L-42) (hereinafter referred to as Compound (L-42)) in which G 4 is C, 1, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX165),
  • Compound (L-42) in which G 4 is CH, R 3c is a hydrogen atom and R 3b is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX166).
  • a compound represented by Formula (L-43) (hereinafter referred to as Compound (L-43)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX169).
  • Compound (L-43) in which G 4 is a nitrogen atom, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 1 to 15 (hereinafter referred to as Compound Group SX171).
  • a compound represented by Formula (L-44) (hereinafter referred to as Compound (L-44)) in which G 4 is CH, R 3b is a hydrogen atom, and R 3c is any one of the substituents described in Tables 7 to 15 (hereinafter referred to as Compound Group SX173).
  • Compound (L-44) in which G 4 is CH, R 3c is a hydrogen atom, and R 3b is any one of the substituents described in Tables 7 to 15 hereinafter referred to as Compound Group SX74).
  • the compound of the present invention may be used in admixture or in combination with one or more ingredients (hereinafter referred to as “the present ingredients”) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d).
  • the present ingredients selected from the group consisting of Group (a), Group (b), Group (c), and Group (d).
  • the admixture or combination means that the compound of the present invention and the present ingredient are used at the same time, separately, or at a time, interval.
  • the compound of the present invention and the present ingredient may each be contained in separate, formulations, or may be contained in one formulation.
  • An aspect of the present invention relates to a composition that contains one or more ingredients (that is, the present ingredients) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the compound of the present invention,
  • Group (a) is a group of insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients which consists of Subgroups a-1 to a-10.
  • Subgroup a-1 Carbamate-based acetylcholinesterase (ACHE) inhibitors
  • Subgroup a-2 Organophosphorus-based acetylcholinesterase (AChE) inhibitors
  • Subgroup a-3 GABAergic chloride ion channel blockers
  • Subgroup a-4 GABAergic chloride ion channel allosteric modulators
  • Subgroup a-6 Nicotinic acetylcholine receptor (nAChR) competitive modulators
  • Subgroup a-7 Ryanodine receptor modulators
  • Subgroup a-8 Microbial materials.
  • Subgroup a-9 Nematicidal active ingredients
  • Subgroup a-10 Other insecticidal active ingredients and acaricidal active ingredients
  • Group (b) is a group of fungicidal active ingredients which consists of Subgroups b-1 to b-18.
  • Subgroup b-1 PA fungicides (phenylamide)
  • Subgroup b-2 MBC fungicides (methylbenzimidazole carbamate)
  • Subgroup b-4 succinate dehydrogenase inhibitors (SDHIs)
  • Subgroup b-5 Qol fungicides (Qo inhibitors)
  • Subgroup b-6 Qil fungicides (Qi inhibitors)
  • Subgroup b-8 AP fungicides (anilinopyrimidine)
  • Subgroup b-9 PP fungicides (phenylpyrrole)
  • Subgroup b-10 AH fungicides (aromatic hydrocarbon)
  • Subgroup b-11 DM1-fungicides (demethylation inhibitors)
  • Subgroup b-12 CCA fungicides (carboxylic acid amide)
  • Subgroup b-13 Piperidinylthiazole isoxazoline
  • Subgroup b-17 Microbial fungicides
  • Subgroup b-18 Other fungicides
  • Group (c) is a group of plant growth-regulating ingredients which consists of Subgroup c-1, Subgroup c-2, and Subgroup c-3.
  • Subgroup c-1 Plant growth-regulating ingredients
  • Subgroup c-2 Mycorrhizal fungi
  • Group (d) is a group of phyototoxicity-decreasing agents.
  • an effect of the composition is expressed depending on a content or a content ratio of the present ingredient or the compound of the present invention in the composition. Therefore, a use of the composition can be determined depending on the effect expressed by the composition.
  • the composition may have one or two or more uses.
  • composition An aspect of the composition is agrochemical composition
  • composition is a harmful-arthropod-controlling composition.
  • composition is an insecticidal, acaricidal- or nematicidal composition.
  • composition is a fungicidal composition.
  • composition is a plant growth-regulating composition.
  • composition is a phytotoxicity-decreasing composition.
  • alanycarb+SX means a combination of alanycarb and SX.
  • the abbreviation SX means “any one compound of the present invention selected from Compound Groups SX 1 to SX 176”.
  • all of the present ingredients as described below are known ingredients which can be obtained from commercially available formulations or can be produced using known methods. In a case were the present ingredient is a microorganism, the microorganism can also be obtained from a microorganism depositary institution. Numbers in parentheses indicate CAS registration numbers.
  • Ethiprole+SX fipronil+SX, flufiprole+SX, chlordane+SX, endosulfan+SX, alpha-endosulfan+SX, and pyriprole+SX.
  • Aizawai QC-91+SX Bacillus thuringiensis subsp. Aizawai Serotype H-7+SX, Bacillus thuringiensis subsp. Kurstaki ABTS351+SX, Bacillus thuringiensis subsp. Kurstaki BMP 123+SX, Bacillus thuringiensis subsp. Kurstaki EG234+SX, Bacillus thuringiensis , subsp, Kurstaki EG 7841+SX, Bacillus thuringiensis subsp. Kurstaki EVB113-19+SX, Bacillus thuringiensis subsp. Kurstaki F810+SX, Bacillus thuringiensis subsp.
  • Kurstaki HD-1+SX Bacillus thuringiensis subsp. Kurstaki PB54+SX, Bacillus thuringiensis subsp. Kurstaki SA-11+SX, Bacillus thuringiensis subsp. Kurstalci SA-12+SX, Bacillus thuringiensis subsp. Tenebriosis NB176+SX, Bacillus thuringiensis subsp. Thuringiensis MPPL002+SX, Bacillus thuringiensis subsp. morrisoni +SX, Bacillus thuringiensis var. colmeri +SX, Bacillus thuringiensis var.
  • aegypti +SX Bacillus thuringiensis var. T36, Bacillus firmus GB-126+SX, Bacillus firmus 1-1582+SX, Bacillus megaterium +SX, Burkhplderia rinojensis A396+SX, Chromobacterium subtsugae PRAA4-IT+SX, Dactyllcla ellipsospora +SX, Dcctylaria thaumasia +SX, Hirsutella rhossiliensis +SX, Hirsutella minnesotensis +SX, Hirsutella thompsonii +SX, Lagenidium gigdnteum +SX, Lecanicillium lecanii KVO 1+SX, Metarhizium anisppliae +SX, Metarhizium anisppliae var.
  • acridum +SX Metarhizium flavoviride +SX, Monacrosporium phytomopagum +SX, Paenibacillus popilliae +SX, Pasteuria nishizawae Pn1+SX, Pasteuria penetrans +SX, Pasteuria usgae +SX, Pesteuria thoynei +SX, Serratia entomophila +SX, Verticillium chlamydosporium +SX, and Verticillium lecani NCIM 1312+SX.
  • Azoxystrobin+SX coumoxystrobin+SX, enoxastrobin+SX, flufenoxystrobin+SX, picpxystrpbin+SX, pyraoxystrobjn+SX, maiidestrobiri+SX, pyraclostrobin+SX, pyrametostrdbin+SX, triclopyricarb+SX, kresoxim-methyl+SX, trifloxystrobin+SX, dimoxystrobin+SX, tenaminstrobin+SX, metominostrobin+SX, orysastrobin+SX, famoxadone+SX, fiupxastrpbin+SX, fenamidone+SX, and pyribencarb+SX.
  • Glomus spp.+SX Glomus intraradices +SX, Glomus mosseae +SX, Glomus aggregatum +SX, and Glomus etunicatum +SX.
  • the compound of the present invention can be used in admixture or in combination with one or more ingredients (hereinafter referred to as present ingredients) selected from the group consisting, of Group (e), Group (f), Group (g), and Group (h).
  • present ingredients selected from the group consisting, of Group (e), Group (f), Group (g), and Group (h).
  • An aspect of the present invention relates to a composition that contains one or more ingredients (that is, the present ingredients) selected from the group consisting of group (c). Group (f), Group (g), and Group (h).
  • harmful arthropods against which the compound of the present invention has an efficacy for example, harmful insects and harmful acarids can be mentioned.
  • harmful arthropods specifically, for example, the following can be mentioned,
  • Hemiptera Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida , and Tagospdes orizicoius ; Cicadellidae such as Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recitia dorsalis, Empoasca qnukii, Empoasca fabae, Dalbulus maidis , and Cofana spectra ; Cercopidae such as Miahanarva posticata and Mahanarva fimbriolata , Aphididae such as Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola,
  • Lepidoptera Crambidae such as Chilo supprcssalis, Darkheaded stem borer ( Chib polychrysus ), White stem borer ( Scirpophaga innotata ), Scirpophaga incertuias, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmiaexigua, Motarcha derogata, Ostrinia fumacalis , European corn borer ( Gstrinia nubilahs ), Tlellula undalis, Herpetogramma luctuosale, Pediasia teterreilus, Nymphula depunctalis , and Sugarcane borer ( Diatraea saccharalis ); Pyralidae such as Elasmopalpus ligndselius, Plodia intcrpunctella , and Euzophera batangensis
  • Heliothis virescens such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea , Velvetbean caterpillar ( Anticarsia gemmatalis ).
  • Cotton leafworm Alabama argillacea
  • Hop vine borer Hydraecia immanis
  • Pieridae such as Pieris rapae
  • Tortricidae such as Graphplita molesta, Gtapholita dimorpha, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxpphyes orana fasciata
  • Adpxpphyes honmai Homona magnanima
  • Archips fuscocupreanus Cydia pomotlella, tetranlpera sdhistaceana .
  • Graciliariidae such as: Caioptilia theiypra and Phyllonorycter ringoniella ; Carpos153ae such as Carposina sasakii ; Lyonetiidae such as Coffee Leaf miner ( Leucoptera coffeela ), Lyonetia clerkella , and Lyonetia prunifoliella ; Lymantriidae, for example, Lymantria spp. such as Lymantria dispar , and Euproctis spp.
  • Euproetis pseudoconspersa Plutellidac such as Plutella xylostella ; Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phtlrorimaea operculclla and Tula absolutea ; Arctiidac such as Hyphantria cunea ; Castniidae such as Giant Sugarcane borer ( Telchin licus ); Cossidae such as Cosus insularis ; Geometridae such as Ascotis selenaria ; Limacodidae such as Parasa lepida ; Stathmopodidae such as Stathmopoda constitutessa ; Sphingidae such as Acherontia lachesis ; Sesiidae such as Nokotia feralis,
  • Thysanoptera Tliripidae such as Frankliniella occidentalism Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stcnchaetothrips biformis , and Echinothrips americanus ; and Phlaeothripidae such as Haplothrips aculeatus.
  • Diptera Anthpmyiidae such as Delia plalura, Delia antiqua , and Pegomya cuniculafia ; Ulidiidae such as Tetanops myopaefomiis ; Agromyzidae such as Agiromyza oryzae, Liriomyza sativae, Uriomyza trifolii , and Chromatomyia horticola ; Chloropidae such as Chlorops oryzae ; Tephritidae such as Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratltis capitata, Rhagolctis pomonella , and Rhacochlaena japonica ; Ephydridae such as Hydrellia griseola, Hydrellia philippina , and Hydrellia
  • Coleoptera Chrysomelidae such as Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae, Diabrotica balteata .
  • Cucurbit Beetle Diabrotica speciosa
  • Cerotoma trifurcata Qulema melanopus.
  • Heptophylla picea European Chafer ( Rhizotrogus majalis ), Tomarus gibbosus. Holotrichia spp, Phyllpphaga spp. such as Phyllophaga crinita , and Diloboderus spp. such as Dilobodems abderus ; Curctilionidae such as Araecerus coffeae, Cylas formicarius.
  • Orthoptera such as Locusta migratoria, Dociostaurus maroecanus, Chortoicetes terminifera, Nlomadacris septemfasciata , Brown Locust ( Locustana pardalina ), Tree Locust ( Anacridium melanorhodon ), Italian Locust ( Calliptamus italicus ).
  • Differential grasshopper Melanoplus differentialis
  • Two striped grasshopper Melanoplus bivittatus
  • Migratory grasshopper Melanoplus sanguinipes
  • Red-Legged grasshopper Melanoplus femurrubrum
  • Hymehoptera Tenthredinidae such as Athalia rosae and Athalia japonica ; Formicidae, for example, Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp.
  • Brown leaf-cutting ant Atta capiguara ), Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Lihepithema humile, Formica firsca japonica, Prjstomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus spp, such as Camponotus japonicus and Camponotus obscuripes, Pogonomyrmex such as Pogonomyrmex occidental is, Wasmania such as Wasmania auropunctata , and Anoplplepis gracilipes ; Vespidae such as Vespa mandarinia japonica, Vespa simillima, Vespa analis Fabriciusi, Vespa velutina , and Polistes jokahamae ; Siricidae such as Urocerus gigas ,
  • Blattodea such as Blattella germanica ;
  • Blattidae such as Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea , and Blatta orientalis ;
  • Termitidae such as Reticulitermes speratus.
  • Coptotermes formosanus Incisitermes minor, Ctyptotermes domesticus, Qdontotermes formosanus, Neotermes koshunensis, Glyptotermes satsuinehsis, Glyptotermcs nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhpuensis, Reticulitennes aniamianus.
  • Reticuliiermes miyatakei Reticulitermes karimdhehsis; Nasutiterines takasagdensis, Pericapriterrnes nitobei, Sinocapritcrmes mushae , and Comitermes cumulans.
  • Siphonaptera Ctenocephalidae felis, Ctenocephalides canis, Pulex irritans, Xeiropsylla cheopis, Tunga penetrans, Echidridphaga gallinacea, Ndsopsyllus fasciatus , and tire like.
  • Phthiraptera Haenratdpinus suis, Haematopinus eurystemus, Dalmalinia ovis, Linognathus seypsus, Pediculus humanis, Pediculuc hunranus corporis, Pediculus humanus hunranus , and Phthiras pubis.
  • Malloplragda Biting lice which are parasitic on chickens such as Dalmalinia bovis and Lipeurus Caponis, Dalmalinia ovis - Trichodectes canis , and Felicola subrostrata.
  • letranychidae such as Tetranyehus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonyehtis citri, Panonyclrus ulmi and Oligonychos spp.
  • Eriophyidae such as Aculops pclekassi.
  • the harmful-arthropod-controlling composition of the present invention contains the compound of the present invention and an inactive carrier.
  • the harmful-arthropod-controlling composition of tire present invention is usually made into a formulation such as an emulsifiable concentrate, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule, an aerosol, a smoking agent, a poison bait, a resin formulation, a shampoo formulation, a pasty formulation, a foam, a carbon dioxide formulation, and a tablet, by mixing the compound of the present invention with an inactive carrier such as a solid carrier, a liquid carrier, and a gaseous carrier, and, as necessary, adding a surfactant and other adjuvants for formulations.
  • an inactive carrier such as a solid carrier, a liquid carrier, and a gaseous carrier
  • compositions may be processed into a mosquito repellent coil, ah electric mosquito repellent mat, a liquid mosquito formulation, a smoking agent, a fumigant, a sheet formulation, a spot-on formulation, or a formulation for oral treatment, and used.
  • the harmful-arthropod-controlling composition of the present invention may be used in admixture with other insecticides, acaricides, nematicides, fungicides, plant growth-regulating agents, herbicides, or synergists.
  • the harmful-arthropod-controlling composition of the present invention contains the compound of the present invention in an amount of usually 0.01% to 95% by weight with respect to a total weight of the harmful-arthropod-controlling composition.
  • fine powders and granular substances such as clays (kaolin day, diatomaceous earth, bentonite, Fubasami clay, acid clay, and the like), synthetic hydrous silicon oxide, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, and the like), and chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, and the like), or die like, and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, and polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resin, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, and the like) can be mentioned.
  • clays kaolin day, diatomaceous earth, bentonite, Fubasami clay, acid clay, and the like
  • liquid carrier for example, water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, and the like), ketones (acetone, methyl ethyl ketone, cyclohexanone, and the like), aromatic hydrocarbons (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, and the like), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, and the like), esters (ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether a
  • gaseous carrier for example, fluorocarbon, butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide gas can be mentioned:
  • nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, and polyethylene glycol fatty acid ester
  • anionic surfactants such as alkylsulfonate, alkylbenzenesulfonate, and alkylsulfate can be mentioned.
  • a fixing agent As the other adjuvants for formulations, a fixing agent, a dispersing agent, a coloring agent, a stabilizer, and the like can be mentioned, and, specifically, for example, casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, and the like), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, and the like), acidic phosphate isopropyl, 2,6-di-tert-butyl-4-methylphenol, and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol) can be mentioned.
  • casein gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, and the like), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol
  • a base material of the resin formulation for example, vinyl chloride-based polymers, polyurethane, and the like can be mentioned.
  • a plasticizer such as phthalic acid esters (dimethyl phthalate, dioctyl phthalate, and the like), adipic acid esters, and stearic acid may be added as necessary to these base materials.
  • the resin formulation can be obtained by kneading the compound of the present invention in the base material using an ordinary kneading machine and then performing molding by injection molding, extrusion molding, press molding, or the like, and, as necessary, can be further processed into a resin formulation having a shape such as a plate, a film, a tape, a net, and a string through steps such as molding and cutting.
  • resin formulations are processed, for example, as animal collars, animal ear tags, sheet formulations, attractant strings, or gardening supports.
  • a base material of the poison bait for example, a cereal powder, vegetable oil, sugar, crystalline cellulose, and the like can be mentioned, and, as necessary, an antioxidant such as dibutylhydroxytoluene and nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an agent which prevents children and pets from eating by mistake such as capsicum powder, a vermin-attracting perfume such as a cheese perfume, an onion perfume, and peanut oil can be added thereto.
  • an antioxidant such as dibutylhydroxytoluene and nordihydroguaiaretic acid
  • a preservative such as dehydroacetic acid
  • an agent which prevents children and pets from eating by mistake such as capsicum powder
  • a vermin-attracting perfume such as a cheese perfume, an onion perfume, and peanut oil
  • a method for controlling a harmful arthropod of the present invention is carried out by applying an effective amount of the compound of the present invention directly to the harmful arthropod and/or to a habitat (plants, soil, indoor spaces, animal bodies, or the like) of a harmful organism. In addition, treatments can be performed on seeds.
  • the method for controlling a harmful arthropod of the present invention is usually used in the form of the harmful-arthropod-controlling composition of the present invention.
  • an application amount thereof is usually 1 to 10,000 g in an amount of the compound of the present invention per 10,000 m 2 .
  • the compound of the present invention is usually applied in an amount range of 0.001 to 100 g per 1 kg of the seeds.
  • the harmful-arthropod-controlling composition of the present invention is usually applied by dilution with water so that an active ingredient concentration is 0.01 to 10,000 ppm.
  • the harmful-arthropod-controlling composition of die present invention is usually applied as it is.
  • formulations or water dilutions thereof may be sprayed directly on harmful arthropods or plants such as crops to be protected from the harmful arthropods, or soil of cultivated land may be treated with these formulations or water dilutions thereof in order to control harmful organisms which inhabit the soil.
  • a resin formulation which is processed into a sheet or a string can also be applied by a method such as winding crops with the resin formulation, stretching the resin formulation in the vicinity of crops, or spreading the resin formulation on soil around crop roots.
  • ah application amount thereof is usually 0.01 to 1,000 mg, per 1 m 2 of a treated area, in an amount of the compound of the present invention, and in a case of being applied to a space, the application amount is usually 0.01 to, 500 mg, per 1 m 3 of a treated space, in an amount of the compound of the present invention.
  • the harmful-arthropod-controlling composition of the present invention is usually applied by dilution with water so that an active ingredient concentration is 0.1 to 10,000 ppm.
  • the harmful-arthropod-controlling composition of the present invention is usually applied as it is.
  • the harmful-arthropod-controlling composition of the present invention can be applied to the animals by known veterinary methods.
  • the composition is administered, for example, by way of a tablet, being mixed in feed, a suppository, and injection (intramuscular, subcutaneous, intravenous, intraperitoneal injections, or the like).
  • the composition is used, for example, by way of spraying an oil solution or aqueous solution, performing a pour-on or spot-on treatment, washing an animal with a shampoo formulation, or putting a resin formulation, which is made into a collar or ear tag, on an animal.
  • an amount of the compound of tire present invention is usually in a range of 0.1 to 1.000 mg per 1 kg of a body weight of an animal,
  • the compound of the present invention can be used as an agent for controlling harmful arthropods in agricultural land such as fields, paddy fields, lawns, and orchards.
  • the compound of the present invention can control harmful arthropods of agricultural land or the like on which plants and the like as mentioned below are cultivated.
  • Farm crops Corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugarbeet, rapeseed, sunflower, sugarcane, tobacco, and the like:
  • solanaceae vegetables eggplant, tomato, green pepper, hot pepper, potato, and the like
  • cucurbitaceae vegetables cucumber, pumpkin, zucchini, watermelon, melon, and the like
  • cruciferae vegetables Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower, and tire like
  • liliaceae vegetables Welsh onion, onion, garlic, asparagus, and the like
  • umbelliferae vegetables carrot, parsley, celery, parsnip, and the like
  • chenopodiaceae vegetables spinach, Swiss chard, and the like
  • labiatae vegetables Japanese mint, mint, basil, and the like
  • strawberry sweat potato, yam, aroid, and the like
  • fruit trees pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince, and the like), stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune, and the like), citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruits, and the like), nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut, and tire like), berry fruits (blueberry, cranberry, blackberry, raspberry, and the like), grape, persimmon, olive, loquat, banana, coffee, date, coconut, and the like;
  • trees other than fruit trees tea, mulberry, flowering trees, street trees (ash tree, birch, dogwood, eucalyptus , ginkgo, lilac, maple tree, oak, poplar, cercis , Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew), and the like.
  • the plants also include genetically modified crops.
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JP7377513B2 (ja) 2019-07-12 2023-11-10 住化エンバイロメンタルサイエンス株式会社 アルゼンチンアリ防除用毒餌剤
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